Process for the production of new derivatives of the arylides of 2.3 hydroxynaphthoic acid



Patented Sept. 1, 1925 UNITED sTAr s- PATENT OFFICE.

G-EQRG KALISCHER, or MAINKUR, NEAR FRANKFORT-ON-THE-MAIN, AND KARL KELLER, or FRANKFORTV-ON-THE-MAIN, GERMANX, ASSIGNORS T0 LEOPOLD cAs- SELLA & co. GESELLSC'HAFT MIT SBESCHRKNKTER HAFTUNG, A CORPORATION or GERMANY.

PROCESS FOR THE PRODUCTION OF NEW DERIVATIVES OF THE ARYLIDES CE 2.3

' HYDROXYNAIPHTHOIC ACID.

No Drawing.

To all whom it may concern.-

Be it known that we, GEORG KALIscHnR,

a citizen of the German Republic, residing at Mainkur, near Frankfort-on-the-Main, Germany, and KARL KELLER, a citizen of the formaldehyde and similar products,

The new compounds are to be used as intermediates for the production of azo dye- Application filed March 24, 1925. Serial No. 18,053.

Example p 80.8 parts meta-nitranilide of 2.3-hydroxynaphthoic'acid are dissolved with 22 parts caustic soda solution (40 B.) and 200 parts hot water. Into the solution, diluted with 300 parts, of water, a solution of 12 parts dextrose in 40 parts water is poured at' 40 about 65 and a temperature of 6070 maintained for 12 hours. From the yellowish brown solution the new product of reduction is advantageously separated as salt of sodium by adding common salt and then in an aqueous suspension converted into the free state by treating with a mineral acid. The raw product may be purified by redissolving it in diluted hot alkaline solution and precipitating again as salt of sodium.

The sym.- bis( 2.3 hydroxynaphthoyl mm-diaminoazoXy-benzene, having the formula:

thus obtained is distinguished from the parent body by its much lesser solubility in organic solvents. It is only very sparingly soluble in glacial acetic acid and monochlorobenzene. crystallized from nitrobenzene it forms .a brownish crystalline powder, dissolving in sulfuric acid with an. intensely yellow color and decomposing above 285 without melting.

Example 2.

If, instead of the meta-nitranilide of 2.3-

hydroxynaphthoic acid, used in example 1, the nitrotoluidide of the formula is subjected to the same treatment, a body of very similar properties is obtained. The quantity of dextrose may vary considerably wherein X means an azo groupN:N- or an azoxy group wherein R means an aryl residue. X an azo group -N:N- or an azoXy group v 2. A process of making new derivatives of the arylides of 2:3-hydroxynaphthoio acid without substantially changing the result, also instead of dextrose, zinc-dust or sulfide of sodium or similar reducing agents may be used.

In the same manner also other nitro derivatives of the arylides of 2.3-hydroxynaphthoic acid can be used, such as the condensation products of 2.3-hydroxynaphthoic acid with metanitro-ortho-anisidine (OCH;- NH 2 :N O. 1 :2 l), ortho-chloro-metanitraniline (Cl: NH :NO :1 2:41), paranitraniline m-nitro-ortho-toluidine (CH NH :NO :1 1'2 5), ortho-chloro-para nitraniline (Cl :NH NO :1: 2: 5), para-nitro-ortho-anisidine (OCH NH NO l 215), chloronitroanisidines ((llzNl-l toCH =No =1=2=e 5 and OCH :NH Cl:- NO l 2 li 5), nitrocresidine (OCH NH CH NO :1 2 4 5) nitroamidohydroquinonedimethylether .(OOH NH z- OCH :NO :1:2:4::5) and others.

The' bodies, obtained therefrom, are derivatives of the arylides of 2.3-hydroxynaphthoic acid of the benzene series, having the general formula:

cording to the methods, customary for the production of aromatic acylamino compounds.

Having now particularlydescribed and ascertained the nature of our said invention and in what manner the same is to be performed, we declare, that what we claim is:

1. As new compounds derivatives of the arylides of 2.3-hydroxynaphthoic acid, having the general formula:

by; treating nitroarylides of 2.3-hydroxynaphthoic acid with reducing agents in an alkaline solution.

3. As new compounds derivatives of the arylides of 2.3-hydroxynaphthoic acid of the benzene series, having the general formula:

wherein X means an azo group --N:N- acid of the benzene series by treating nitroor azoxy group v arylides of 2.3-hydroxynaphthoic acid of the -N4N, benzene series with reducing agents in an 1 \O/ alkaline solution.

Y hydrogen or a'monovalent 'substituent. 5. As a new compound the sym.-bis- 4. A process of making new derivatives hydroxynaphthoyllemeta -meta diamldoof the arylides of 2.3-hydroxynaphthoic azoxybenzene, having probably the formula:

on no Q0-NHQ ONE-O0 6. A process of making a new derivative In witness whereof we have hereunto 20 of the arylides of. 2.3-hydroxynaphthoic signed our names this eleventh day of acid by treating the meta-nitranilide of 2.3- March, 1925. 1 t hydroxynaphthoic acid with reducing agents GEORG KALISGHER. in an alkaline solution. KARL KELLER. 

